Optically active carboxylic acid esters are used in various fields such as pharmaceutical products, intermediates of biologically active substances, intermediates of natural product synthesis, and the like.
Conventionally, as a method for manufacturing optically active carboxylic acid esters, a method has been known by way of reaction between an alcohol and carboxylic acid using an asymmetric catalyst.
As a method for manufacturing an optically active carboxylic acid ester as well as an optically active alcohol, a method has been known that uses tetramisole or benzotetramisole as a catalyst, and produces the optically active carboxylic acid ester from a racemic secondary benzyl alcohol in the presence of an acid anhydride (see Non-Patent Document 1). In addition, a method for manufacturing an optically active carboxylic acid ester from a racemic propargylic alcohol in the presence of an acid anhydride using benzotetramisole as a catalyst has been known (see Non-Patent Document 2). Furthermore, a method for manufacturing an optically active carboxylic acid ester by reacting a racemic secondary alcohol and a carboxylic acid in the presence of a benzoic anhydride or a derivative thereof, using tetramisole or benzotetramisole as a catalyst has also been known as a method improving substrate universality (see Patent Document 1).
On the other hand, a method for manufacturing an optically active carboxylic acid ester by reacting a racemic carboxylic acid and an alcohol in the presence of a benzoic anhydride or a derivative thereof, using tetramisole or benzotetramisole as a catalyst has also been known as a method for manufacturing an optically active carboxylic acid ester along with an optically active carboxylic acid (see Patent Document 2).    Patent Document 1: PCT International Publication No. WO2008/140074    Patent Document 2: PCT International Publication No. WO2009/113428    Non-Patent Document 1: Birman, V. B.; Li, X.; Org. Lett.; 2006, 8, (7), p. 1351-1354    Non-Patent Document 2: Birman, V. B.; Guo, L.; Org. Lett.; 2006, 8, (21), p. 4859-4861    Non-Patent Document 3: Ebbers, E. J. et al.; Tetrahedron; 1997, 53, (28), p. 9417-9476